Almost Fearless

The Mental Shift to Begin the Redesign: Day 1 of 30w30d

This post is part of 30 Ways in 30 days to Redesign Your Life and Travel the World. This series seeks to give you the practical, real world steps you need to take to get from wherever you are, to exactly where you want to be– traveling the world and living the lifestyle you want.


30 ways in 30 Days, mentality, change, roadblocks, around the world trips

If you’re thinking of ways to travel the world, you might have wondered: how do you go from planning to actually making it happen?  What’s crucial step from wanting to travel to suddenly just doing it?

Only 2 years ago, I didn’t know.  I would study travel blogs, trying to fit how their steps into my own circumstances.  I’d re-read “How it feels” posts trying to find some clues as to what it is really like to give up everything to travel and summon my own courage.  I’d research residency visa requirements to countries that I’d like visit.  I’d make budgets, dream itineraries, research flight costs– important research but it can’t go on forever.

Eventually, I just made the decision to go– honestly committing myself to redesigning my life and traveling in the next six months– a simple but difficult step.  I had set a date.  Finally making the decision changed everything.

Here’s your test: When are you leaving?

If you have a date, congrats, you are well on your way.  Sure there are lots of details to work out, but you’ve already completed the hardest part: the first step.

For those of you who don’t have a date, here’s where it gets tricky.  When does research to make sure it’s possible, become a roadblock in and of itself?  If you’re not careful the problem becomes:

  • You can’t take the leap until you’re sure it will work out
  • You won’t know until you take the leap

In other words, anyone that waits for a guarantee, waits forever.  It’s not coming.

Today, I’m asking everyone to take a small step with me and change their expectations from finding what will definitely work to probably will.

Yes, there is inherent risk in redesigning your life and traveling the world.  But I’d also caution that there is inherent risk in everything that we do.  Buying a house is placing a bet that you won’t be laid off or the market won’t crash, leaving you 25% underwater on your mortgage.  Taking a job is placing your short term financial future in the hands of an employer that you don’t know very well.  Placing your money in retirement accounts is a statement that you feel pretty confident that you won’t need that money this week to survive.  But how do you really know?

The answer: we never know.

I’m not asking anyone to put their financial future, careers, spouse, children or pets at undue risk.  Rather that you change your thinking as you research your options, from looking for the “absolutely, fails-safe, must work” to “reasonable to assume, others have done it” as your trigger to take the plunge.  The same as you would for anything in your life.

Then you must set a date.

Breaking your own rules

The second step is to become a diligent rule breaker.  Every time you say to yourself, “I can’t do that, because…” I want you to ask yourself why.  For example:

  • I have a dog and I can’t bring it with me and I can’t leave it behind
  • I can’t travel with my kids
  • I know everyone says this, but I really can’t save any money

There are people who travel with their pets, take their kids abroad and make an art form out of living cheaply to save for travel.  So why can’t you?  Why have you set that rule?  When you set a rule for yourself, you’ve just changed a problem into a deal breaker.  Unless someone alters the space-time continuum and makes it possible to neither bring nor leave your pet at the same time as you travel, you’re effectively closed the door.  Problems we can deal with.  Huge amounts of debt?  Empty savings account?  No ideas of where to start?  All fixable.  Breaking the laws of physics? Not so much.

The goal is to not live by rules you’ve inadvertently set for yourself.  Instead of pre-emptively deciding that it’s impossible, release yourself from controlling the outcome and try to get to the core of your concern.  For example:

  • How can I ensure my dog is comfortable and happy when we travel together?
  • How can I travel with my kids and stay sane, afford it and maintain their schooling?
  • What are some ways I can raise the cash to travel?

After you answer these questions, you may decide that the trade offs aren’t worth it.  But it will be an informed decision.  You will make the choice, not your initial fear/reluctance/negativity.

Your homework:

1.  Write down every item that is preventing you from traveling right now.  As we go through this month, we will be (hopefully) crossing those items out.  This is your to-do list.

2.  Go through your list.  Have you created any impossible barriers?  Have you set an impossible rule for yourself?  Try re-wording the problem in a way that addresses your core concern without jumping to conclusions about the outcome.

3.  Start thinking about a date.  If you’re not ready yet, that’s okay, but you might set a soft date based on the items on list #1, based on how your estimate to address each item.  As you go through the month, adjust the date as you get closer to working out all of your details.

4.  All month: Keep me honest!  If you need more information on any topic, as we cover them, let me know in the comments.  I try to anticipate as many different scenarios as possible, but if I’m not addressing yours, contact me.  You can also email me privately at

Additional Reading:

A New Era of Retirement

Why You Should Quit Your Job and Travel the World

Breaking Out of the “8” Life

Should, Should, Should I Travel?

An Introduction (making the decision)

Christine Gilbert

I’ve been dragging my husband around the world since 2008 always with the promise that, “Yes, Drew there will definitely be hammocks there.”



  • Thanks for this awesome post! I feel like I’ve been planning for a big trip all through college; when will the planning end? I just need to do it.

    You wouldn’t happen to be a Smithie, would you? One of your references to the Haymarket got me curious… anyway, I look forward to the other 29 ways! And congratulations on the baby!
    .-= Laura´s last blog ..The sensitive plant =-.

  • We’re about to embark on three months in Beijing with our two young kids (ages 3.5 and 2). Having a date helped us a lot: we had a window of opportunity while my husband is on parental leave, since I can work remotely. It also helped to tell people about our dream, which made it seem more real and put on some pressure to actually go! A month before, we didn’t have all the details worked out, but we bought the airline tickets and committed ourselves.

    Looking forward to the rest of this series … and to seeing how you’ll transition to traveling with a kid, Christine. Congrats 🙂
    .-= Alison Gresik´s last blog ..Heaven, I’m in Heaven =-.

  • Something I love about making the list is that, at least for me, it ends up having less items on it than anticipated. You go to write something down and instead catch yourself saying, “Well that isn’t REALLY keeping me from doing anything.” In the process of writing it down you will have already crossed off several things on the list in your head.

    I chose the date a couple months ago [03/11/2010] and can’t wait.
    .-= Caleb´s last blog ..Lobster Mac & Truffle Cheese =-.

  • We are coming up on our one-year anniversary of making the decision to travel. What started out as a “what if” question over margaritas with friends quickly became real with us. We started the research the next day and set our departure date within that first month.

    Our timeline was 2 years, mainly due to saving money, but the funny thing is that we are going to hit our financial goal by the end of this month, almost a year ahead of schedule. I am amazed at how easy it has been to save money because what it will buy us later is so much more than anything we could buy now. And now that we are ahead of schedule on saving we’ll be able to stay gone longer. And THAT is very good news!

    Our date is October 1, 2011. I can’t wait to read the rest of your series (and congrats on the pregnancy – if SoulTravelers3 can travel long-term with a kid, so can you!)
    .-= Betsy Talbot´s last blog ..Going from Vacation to Work without Losing Your Zen =-.

  • What an inspiring post. Although I travel often, it’s got me thinking about my dream of relocating to another country. I took most of the steps you outlined when my daughter was young but discovered the country I wanted to move to had bad schools, hospitals and crime. Now that my kids are older, there’s no reason to start the steps again, except that it’s so scary.I will be re-thinking my plan along with your posts.
    .-= Fly Girl´s last blog ..Summer In the (Chi) City =-.

  • Christine… this series could not come at a better time! Though were not aiming to travel the world (yet!), my husband and I ARE aiming to make a change and start a couple businesses. We have just started to discuss the date, and the plan. I CANNOT WAIT to read the rest of this series this month! It will be applied, daily.

    The one thing I have noticed is… now that we have focus, and a time frame, it’s feeling like it’s not only do-able, but that it may be do-able in a shorter time frame that we originally gave ourselves!
    .-= Lori´s last undefined ..If you register your site for free at =-.

  • The mental shift is the most important part for me…..the “voices in my head” have been holding me back most of my life….

    I have the plan in place just one major obstacle which I indicated in another comment hubby is about 8000-9000 upside down in a car……..

    kids schooling is covered…stopped spending on the stuff that kept us where we are for 17 years ———– now the car issue……

    I am already telecommuting at present as a transcriptionist and hubby will be on disability for a bit

    Luv luv this series

  • Awesome Christine, love the the concept of 30 Ways in 30 Days — will follow closely. Happy to see that Kathryn and I are on the right track so far! We’ve picked a date and keep an eye on it via our blog! One year, nine months and 27 days as of the time of this comment!

  • We’re honored to be on your reading list Christine. Setting the date made it very real for us as well. We set a time-frame on the same day we decided to travel for a year. It was quite a conversation we had that day!! Traveling with the kids wasn’t a big decision at all because we already home schooled. We’ve been on the road for three months, and it’s challenging and awesome and beautiful and crazy. We’ve never been closer as a family, and our children are getting an educational experience unlike anything I had!
    I know this series will inspire and help other people to take the leap and live the dream. ANY dream!!! We applaud you!
    Bob & Brenna
    .-= Brenna Gibson Redpath´s last blog ..Killer Bat Attack =-.

  • Very inspiring – thank you. I’d be interested in advice/thoughts on how to plan for the return. I actually have enough cash saved to travel for awhile. My block is the concern that I won’t find a job when I get back. Also dealing with family objections. This is funny coming from me, because I did take off and backpacked for 6 months 12 years ago. It was rather stressful finding work on my return but I did eventually. Guess I need dose of “it’ll work out” from you! 🙂
    .-= Robyn´s last blog ..Appalachian Trail Video =-.

  • […] over at Almost Fearless has started a new project in the last couple weeks.  ”Thirty Ways in Thirty Days to Redesign your Life and Travel the World” is a series of posts designed to teach you how to do just that.  So far she has looked at a […]

  • hello I am very excited to find your web site. For years I have been trying to figure out how to travel in Italy/ Europe and still pay off my student loan. I have no kids, no pets, I dont even have a lease on an apartment. I’m just trying to find a way to live and work in Sicily and also learn the language. I have been a chef for many years and love to experience food and other cultures. Any ideas or tips to get this project off the ground??
    Thanks so much I hope to hear from you soon!
    chef Melanie

  • Hi Christine,

    You’ve titled your blog very appropriately. I commend you for your bravery, and for not only inspiring others to pack their bags and see the world, but for the thoughtful thorough practical approach that you take addressing all of the logistics and hindrances that may prevent people from doing what you have…

    Bon Voyage,


  • I am sure you are inspiring many to set a date, which also means creating goals. Hey, I used to be a freelancer for real in the offline world, but got lost in taking it online. All things are doable.

    We are at square one with the first post. Can we do it in 30 days? Let’s give it a shot.
    .-= Telecommute Jobs´s last blog ..Can one supplement their income by playing internet poker? =-.

  • […] Gilbert of Almost Fearless is running a series called 30 Ways in 30 Days to Redesign Your Life and Travel the World.   The first post talks about the mental shift to begin the redesign.  This is one thing we did […]

  • Very informative and enlightening article. It makes me really think seriously about quitting my job and to take up trevelling, which is my passion.

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